Cyanogen Bromide → HCID 9932309, compound

Participants

Reaction Steps

To a solution of 3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid hydrazide (0.806 g, 2 mmol) in 5 ml of dioxane was added cyanogen bromide (0.212 g, 2 mmol) followed by a solution of sodium bicarbonate (0.17 g, 2 mmol) in 5 ml of water. The resulting mixture was stirred 18 ours at room temperature. The solution was concentrated and the residure was run column with hexanes/ethyl acetate (3/1) to give the product which was recrystallized from ethyl acetate/hexanes to provide a pale-yellow crystal. The yield: 58% m.p. 183.7-184.0° C. 1H NMR(CDCl3, 400 Hz): /ppm 8.87(1H, s, —NH—); 7.52(1H, s, Phenyl-H); 7.45-7.49(1H, m, Phenyl-H); 7.40(1H, d, J=8.3 Hz, Phenyl-H); 6.77-6.83(1H, m Phenyl-H); 6.60-6.63(1H, m, Phenyl-H); 5.02(2H, s, —NH2), 2.36(3H, s, CH3)

Provenance & Evidence